Process for producing an esterified alkoxylated polyol

Abstract

A method of obtaining a fatty acid-esterified alkoxylated polyol useful as a reduced calorie fat substitute is provided. The method utilizes a C 1 -C 4 alkyl ester of a C 8 -C 24 fatty acid such as methyl stearate or methyl oleate and a short chain acid-esterified alkoxylated polyol such as the acetate of propoxylated glycerin as reactants.

We claim: 
     
       1. A process for the preparation of a fatty acid-esterified alkoxylated polyol, wherein said process comprises reacting a C 1  -C 4  alkyl ester of a C 8  -C 24  fatty acid with a short chain acid-esterified alkoxylated polyol in the presence of a basic catalyst in a reaction zone at a temperature effective to simultaneously form the fatty acid-esterified alkoxylated polyol and a C 1  -C 4  alkyl ester of a short chain acid with said C 1  -C 4  alkyl ester of the shod chain acid being removed from the reaction zone during said reacting. 
     
     
       2. The process of claim 1 wherein the C 1  -C 4  alkyl ester of a C 8  -C 24  fatty acid is a methyl or ethyl ester. 
     
     
       3. The process of claim 1 wherein the C 1  -C 4  alkyl ester of a C 8  -C 24  fatty acid is a C 1  -C 4  alkyl ester of a fatty acid selected from caproic acid, pelargonic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, lignoceric acid, behenic acid, isostearic acid, oleic acid, palmitoleic acid, lidoleic acid, linolenic acid, arachidonic acid, eleostearic acid, eicosenoic acid, elaidic acid, erucic acid, arachidic acid, margaric acid, undecylic acid, pentadecanoic acid, and mixtures thereof. 
     
     
       4. The process of claim 1 wherein the short chain acid-esterified alkoxylated polyol is an acetic acid-esterified alkoxylated polyol. 
     
     
       5. The process of claim 1 wherein the short chain acid-esterified alkoxylated polyol is a shod chain acid-esterified propoxylated glycerin. 
     
     
       6. The process of claim 1 wherein the short chain acid-esterified alkoxylated polyol is obtained by alkoxylation of a polyol having from 3 to 8 hydroxyl groups selected from C 3  -C 12  aliphatic triols, C 4  -C 12  aliphatic tetrols, C 5  -C 8  sugar alcohols, monosaccharides, disaccharides, alkyl glycosides, and glycerol oligomers with at least one epoxide selected from ethylene oxide, propylene oxide, and 1,2-butene oxide to form an alkoxylated polyol and esterification of the alkoxylated polyol with a C 2  -C 4  carboxylic acid or equivalent thereof. 
     
     
       7. The process of claim 1 wherein the amount of the C 1  -C 4  alkyl ester of the C 6  -C 24  fatty acid is equal to 0.8 n to 1.2 n moles per mole of short chain acid-esterified alkoxylated polyol wherein n is an integer of from 3 to 8 and is equal to the number of short chain acid ester groups on the short chain acid-esterified alkoxylated polyol. 
     
     
       8. The process of claim 1 wherein the basic catalyst is a sodium or potassium alkoxide. 
     
     
       9. The process of claim 1 wherein the temperature is from 70° C. to 160° C. 
     
     
       10. The process of claim 1 wherein the basic catalyst is present at a concentration of from 0.01 to 3 weight percent based on the total weight of C 1  -C 4  alkyl ester of the C 8  -C 24  fatty acid and short chain acid-esterified alkoxylated polyol. 
     
     
       11. The process of claim 1 wherein said C 1  -C 4  alkyl ester of the short chain acid is removed from the reaction zone in vapor form by distillative means. 
     
     
       12. A process for the preparation of a fatty acid-esterified alkoxylated polyol, wherein said process comprises reacting a methyl or ethyl ester of a C 8  -C 24  fatty acid with an acetic acid-esterified alkoxylated polyol, said acetic acid-esterified alkoxylated polyol being obtained by alkoxylation of a polyol having from 3 to 8 hydroxyl groups selected from C 3  -C 12  aliphatic triols, C 4  -C 12  aliphatic tetrols, C 5  -C 8  sugar alcohols, monosaccharides, disaccharides, alkyl glycosides and glycerol oligomers with at least one epoxide selected from ethylene oxide, propylene oxide, or 1,2-butene oxide to form an alkoxylated polyol and esterification of the alkoxylated polyol with acetic acid or an equivalent thereof, in the presence of a sodium or potassium alkoxide catalyst in a reaction zone at a temperature of from 70° to 160° C. to simultaneously form the fatty acid-esterified alkoxylated polyol and a methyl or ethyl ester of acetic acid with said methyl or ethyl ester of acetic acid being removed in vapor form from the reaction zone by distillative means during said reacting. 
     
     
       13. The process of claim 12 wherein the polyol is glycerin. 
     
     
       14. The process of claim 12 wherein the epoxide is propylene oxide. 
     
     
       15. The process of claim 12 wherein the sodium or potassium alkoxide catalyst is sodium or potassium methoxide. 
     
     
       16. The process of claim 12 wherein the amount of the methyl or ethyl ester of the C 8  -C 24  fatty acid is equal to about n moles per mole of acetic acid-esterified alkoxylated polyol, wherein n is an integer of from 3 to 8 and is equal to the number of short chain acid ester groups on the acetic acid-esterified alkoxylated polyol. 
     
     
       17. The process of claim 12 wherein at least 90% of the acetic acidesterified alkoxylated polyol is reacted. 
     
     
       18. The process of claim 12 wherein the methyl or ethyl ester of the C 8  -C 24  fatty acid is obtained by alcoholysis of a triglyceride. 
     
     
       19. The process of claim 18 wherein the triglyceride is obtained from a natural lipid selected from soybean oil, corn oil, cottonseed oil, olive oil, peanut oil, palm oil, palm kernel oil, coconut oil, rapeseed oil, safflower oil, butter, lard, tallow, cocoa butter or fully or partially hydrogenated derivatives thereof. 
     
     
       20. The process of claim 12 wherein the amount of the epoxide is from n to 10 n moles per mole of polyol wherein n is equal to the number of hydroxyl groups on the polyol. 
     
     
       21. The process of claim 12 wherein the concentration of the methyl or ethyl ester of acetic acid is maintained below 5% by weight. 
     
     
       22. The process of claim 12 wherein at least 30 mole percent of the C 8  -C 24  fatty acid is a C 20  -C 24  saturated linear fatty acid. 
     
     
       23. An integrated process for producing a fatty acid-esterified alkoxylated glycerin, wherein said process comprises the steps of (a) reacting a fatty acid triglyceride with a C 1  -C 4  alcohol at a temperature effective to simultaneously form glycerin and a C 1  -C 4  alkyl ester of a C 8  -C 24  fatty acid;   (b) separating the C 1  -C 4  alkyl ester of the C 8  -C 24  fatty acid and the glycerin;   (c) reacting the glycerin with a C 2  -C 10  epoxide to form an alkoxylated glycerin;   (d) reacting the alkoxylated glycerin with an anhydride of a shod chain acid to simultaneously form a shod chain acid-esterified alkoxylated polyol and a shod chain acid;   (e) separating the shod chain acid-esterified alkoxylated polyol from the shod chain acid;   (f) reacting the C 1  -C 4  alkyl ester of the C 8  -C 24  fatty acid with the short chain acid-esterified alkoxylated glycerin in the presence of a basic catalyst in a reaction zone at a temperature effective to simultaneously form the fatty acid-esterified alkoxylated glycerin and a C 1  -C 4  alkyl ester of the shod chain acid, with said C 1  -C 4  alkyl ester of the shod chain acid being removed from the reaction zone during said reacting.